Phenyl azabicyclohexanones

Abstract

Substituted phenyl azabicyclohexanones, their method of preparation, and their conversion into substituted phenyl azabicyclohexanes which are active anxiolytic and analgesic agents.

We claim: 
     
       1. An optically active compound of the formulae: ##STR5## wherein the phenyl moiety is unsubstituted, mono- or di-substituted from the group consisting of halogen, straight chain C 1  -C 6  alkyl, C 1  -C 6  alkoxy, nitro, amino, trifluoromethyl, acetamido and hydroxy; and the racemic mixture thereof. 
     
     
       2. an optically active compound according to Claim 1, wherein the phenyl moiety is di-substituted from the group consisting of halogen, straight chain C 1  -C 6  alkyl, C 1  -C 6  alkoxy, trifluoromethyl, nitro, amino, acetamido and hydroxy. 
     
     
       3. An optically active compound according to Claim 1, wherein the phenyl moiety is unsubstituted or mono-substituted from the group consisting of halogen, straight chain C 1  -C 6  alkyl, C 1  -C 6  alkoxy, trifluoromethyl, nitro, amino, acetamido and hydroxy. 
     
     
       4. An optically active compound according to Claim 3, wherein the phenyl moiety is para or meta substituted from the group consisting of straight chain C 1  -C 6  alkyl, halogen and trifluoromethyl. 
     
     
       5. An optically active compund according to Claim 4, wherein the phenyl moiety is para or meta substituted from the group consisting of methyl, ethyl, chloro, fluoro, bromo and trifluoromethyl. 
     
     
       6. The optically active compound according to Claim 1, 1-phenyl-3-azabicyclo[3.1.0]hexan-2-one. 
     
     
       7. The optically active compound according to claim 1, 1-p-chlorohpenyl-3-azabicyclo hexan-2-one. 
     
     
       8. The optically active compound according to claim 1, 1-phenyl-3-azabicyclo[3.1.0]hexan-4-one. 
     
     
       9. The optically active compound according to claim 1, 1-(p-tolyl)-3-azabicyclo[3.1.0]hexan-2-one. 
     
     
       10. The optically active compound according to claim 1, 1-(p-tolyl)-3-azabicyclo[3.1.0]hexan-4-one. 
     
     
       11. A method for the preparation of an optically active compound of the formulae: ##STR6## wherein the phenyl moiety is unsubstituted, mono- or di-substituted from the group consisting of halogen, straight chain C 1  -C 6  alkyl, C 1  -C 6  alkoxy, nitro, amino, trifluoromethyl, acetamido and and the racemic mixture thereof; which comprises reducing a phenyl cyano ester of the formulae: ##STR7## wherein the phenyl moiety is unsubstituted, mono- or di-substituted as previously defined and R is selected from the group consisting of C 1  -C 6  alkyl; with diborane, in a solvent, at a temperature from about 0° to about 60° C., from about one to about three hours; and reacting the intermediate reduction product with a mineral acid. 
     
     
       12. A method according to Claim 11, wherein said solvent is tetrahydrofuran, and said mineral acid is 6N hydrochloric acid.